University of Groningen
Confined molecular machines and switches
Danowski, Wojtek
DOI:
10.33612/diss.97039492
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Publication date: 2019
Link to publication in University of Groningen/UMCG research database
Citation for published version (APA):
Danowski, W. (2019). Confined molecular machines and switches. Rijksuniversiteit Groningen. https://doi.org/10.33612/diss.97039492
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I
Confined Molecular
Machines and Switches
II The work described in this thesis was carried out at the Stratingh Institute for Chemistry, University of Groningen, The Netherlands.
This work was financially supported by the Netherlands Organization for Scientific Research (NWO-CW, NWO-Top Grant).
Printed by Ipskamp Drukkers BV, Enschede, The Netherlands ISBN: 978-94-034-1972-5 (Printed Version)
III
Confined Molecular Machines and Switches
Proefschrift
ter verkrijging van de graad van doctor aan de Rijksuniversiteit Groningen
op gezag van de
rector mangificus prof. dr. C. Wijmenga en volgens besluit van het College voor Promoties.
De openbare verdediging zal plaatsvinden op
vrijdag 27 september 2019 om 14.30 uur
door
Wojciech Danowski
born on 06 April 1990 in Bialystok, Poland
IV Supervisors Prof. dr. B. L. Feringa Prof. dr. P. Rudolf Co-supervisor Dr. S. J. Wezenberg Beoordelingscommissie Prof. dr. M. Tromp Prof. dr. R. J. M. Nolte Prof. dr. ir. A. J. Minnaard
V
Table of Content
Chapter 1
Photoresponsive Porous Materials ... 1
1.1 Introduction ... 2
1.2 Photoresponsive Molecules ... 4
1.3 Photoresponsive Solid Porous Materials ... 9
1.4 Applications of Photoresponsive Solid Porous Materials ... 10
1.5 Conclusions ... 31
1.6 Aim and Outline of this Thesis ... 33
1.7 References ... 35
Chapter 2 Unidirectional Rotary Motion in a Metal Organic Framework ... 41
2.1 Introduction ... 42
2.2 Synthesis ... 43
2.3 Design, synthesis and characterization of the Motorized Metal Organic Frameworks... 45
2.4 Photochemical and thermal isomerization in solution ... 51
2.5 Photochemical and thermal isomerization in the solid state ... 56
2.6 Conclusions ... 60
2.7 Acknowledgments ... 60
2.8 Experimental Data ... 60
2.9 References ... 72
Chapter 3 Visible Light Driven Rotation of Molecular Motor in a Dual‐Function Metal Organic Framework Enabled by Energy Transfer ... 75
3.1 Introduction ... 76
3.2 Design, synthesis and characterisation of Motorized Metal Organic Framework ... 77
3.3 Energy transfer, photochemical and thermal isomerization in solution ... 85
3.4 Energy transfer, photochemical and thermal isomerization in solid state .... 89
3.5 Conclusions ... 91
3.6 Acknowledgments ... 91
3.7 Experimental Data ... 91
VI
Chapter 4
Modulation of porosity in a solid switchable aromatic framework enabled by
bulk isomerization of an overcrowded alkene ... 101
4.1 Introduction ... 102
4.2 Synthesis of Porous Switchable Frameworks ... 103
4.3 Photochemical and thermal isomerization in solution ... 107
4.4 Photochemical isomerization in the solid state ... 109
4.5 Photomodulation of porosity and gas adsorption of the material ... 112
4.6 Conclusions ... 113
4.7 Acknowledgments ... 114
4.8 Experimental Data ... 114
4.9 References ... 121
Chapter 5 Control over Surface Wettability by Surface‐Immobilised 1st Generation Molecular Motors ... 125
5.1 Introduction ... 126
5.2 Synthesis ... 128
5.3 Photochemical and thermal isomerization in solution ... 130
5.4 Surface functionalization ... 136 5.5 Conclusions ... 139 5.6 Acknowledgments ... 140 5.7 Experimental Data ... 140 5.8 References ... 147 Chapter 6 Towards a photo-switchable molecular rectifier ... 151
6.1 Introduction ... 152
6.2 Design of the rectifier ... 153
6.3 Synthesis ... 157
6.4 UV/Vis and 1H NMR analysis ... 159
6.5 Studies on Surface ... 163
6.6 Conclusions ... 164
6.7 Acknowledgments ... 164
6.8 Experimental Section ... 165
VII
Chapter 7
Maximized change in water contact angle for photoswitchable
cucurbit[8]uril‐mediated supramolecular monolayers on gold ... 173
7.1 Introduction ... 174
7.2 Synthesis ... 176
7.3 Photochemical isomerization studies in solution ... 177
7.4 Surface functionalization ... 181
7.5 Photochemical isomerization studies on surface ... 183
7.6 Conclusions ... 186 7.7 Acknowledgments ... 187 7.8 Experimental Data ... 187 7.9 References ... 198 Chapter 8 Summary ... 203 8.1 Summary ... 204 8.2 Samenvatting ... 208 Acknowledgment Acknowledgment ... 213
